Rational design of a ligand-based antagonist of jasmonate perception

Nat Chem Biol. 2014 Aug;10(8):671-6. doi: 10.1038/nchembio.1575. Epub 2014 Jul 6.

Abstract

(+)-7-iso-Jasmonoyl-L-isoleucine (JA-Ile) regulates developmental and stress responses in plants. Its perception involves the formation of a ternary complex with the F-box COI1 and a member of the JAZ family of co-repressors and leads to JAZ degradation. Coronatine (COR) is a bacterial phytotoxin that functionally mimics JA-Ile and interacts with the COI1-JAZ co-receptor with higher affinity than JA-Ile. On the basis of the co-receptor structure, we designed ligand derivatives that spatially impede the interaction of the co-receptor proteins and, therefore, should act as competitive antagonists. One derivative, coronatine-O-methyloxime (COR-MO), has strong activity in preventing the COI1-JAZ interaction, JAZ degradation and the effects of JA-Ile or COR on several JA-mediated responses in Arabidopsis thaliana. Moreover, it potentiates plant resistance, preventing the effect of bacterially produced COR during Pseudomonas syringae infections in different plant species. In addition to the utility of COR-MO for plant biology research, our results underscore its biotechnological potential for safer and sustainable agriculture.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Amino Acids / metabolism
  • Amino Acids / pharmacology
  • Amino Acids, Neutral / pharmacology*
  • Anthocyanins / metabolism
  • Arabidopsis / drug effects
  • Arabidopsis / metabolism
  • Arabidopsis / microbiology
  • Arabidopsis Proteins / antagonists & inhibitors
  • Arabidopsis Proteins / genetics
  • Arabidopsis Proteins / metabolism
  • Botrytis / pathogenicity
  • Cyclopentanes / metabolism*
  • Cyclopentanes / pharmacology
  • DNA-Binding Proteins / antagonists & inhibitors
  • DNA-Binding Proteins / metabolism
  • Drug Design
  • Gene Expression Regulation, Plant
  • Indenes / chemistry*
  • Indenes / metabolism
  • Indenes / pharmacology
  • Isoleucine / analogs & derivatives
  • Isoleucine / metabolism
  • Isoleucine / pharmacology
  • Ligands
  • Oximes / pharmacology*
  • Oxylipins / metabolism*
  • Plant Roots / growth & development
  • Plant Roots / metabolism
  • Plants, Genetically Modified
  • Pseudomonas syringae / pathogenicity
  • Repressor Proteins / genetics
  • Repressor Proteins / metabolism
  • Transcription Factors / antagonists & inhibitors
  • Transcription Factors / metabolism

Substances

  • Amino Acids
  • Amino Acids, Neutral
  • Anthocyanins
  • Arabidopsis Proteins
  • CONSTANS protein, Arabidopsis
  • Cyclopentanes
  • DNA-Binding Proteins
  • Indenes
  • JAZ9 protein, Arabidopsis
  • Ligands
  • Oximes
  • Oxylipins
  • Repressor Proteins
  • Transcription Factors
  • coronatine-O-methyloxime
  • jasmonoyl-isoleucine
  • Isoleucine
  • coronatine
  • jasmonic acid

Associated data

  • GEO/GSE56027
  • PubChem-Substance/183814155
  • PubChem-Substance/183814156
  • PubChem-Substance/183814157